Photo-ODIBO-EG4-NHS

Photo-DIBO-EG4-SH for strain-promoted alkyne-azide cycloaddition (SPAAC) applications.

Highlights:

  • The only reagent on the market that permits photo-SPAAC ligation
  • Especially engineered for the production of particles and surfaces with spatially resolved chemical functionality, of interest to many areas of science and technology including the fabrication of biochips, microfluidic devices, targeted drug delivery, MEMS and NEMS
  • Photo-ODIBO moiety does not react with organic or inorganic azides, thiols, water, and other endogenous nucleophiles, even at elevated temperatures
  • Equipped with amine-reactive NHS group for easy derivatization of peptides, proteins, and tissues
  • Upon mild UVA irradiation releases azide-reactive ODIBO, the most reactive SPAAC reagents on the market
  • Permits spatially-resolved conjugation using SPAAC, SPANC, SPANOC, IEDDA, and thiol-yne conjugations
  • Long shelf life in the dark

Precursors in the study of strain-promoted alkyne-azide cycloaddition (SPAAC), SPANC, Diels-Alder, and thiol-yne reactions cell and tissue labeling, surface modifiers, chemical synthesis, homo- and hetero-nuclear π metastasis reactions, light-selective labeling, photo-patterning, triazole synthesis, azide quenching reactions.

From the laboratory of Vladimir V. Popik, PhD, University of Georgia.

Catalog Number Product Size AVAILABILITY Price Qty
EGA258
Photo-ODIBO-EG4-NHS
25mg In stock
Price: $438.00
Specifications
Product Type: Small Molecule
Name: Photo-ODIBO-EG4-NHS; Photo-ODIBO-TEG-NHS
Alternative Name(s): 2-(2-(2-(2-((3-(tert-butyl)-1-oxo-1,7- dihydrodibenzo[b,f]cyclopropa[d]oxocin-9- yl)oxy)ethoxy)ethoxy)ethoxy)ethyl (2,5-dioxopyrrolidin- 1-yl) carbonate
Chemical Formula: C33H37NO11
CAS number: 2095777-51-6
Molecular Weight: 623.65
Format: Colorless oil
Purity: >99% 1HNMR
Solubility: CH3CN, MeOH, etc.
Spectral Information: 1H-NMR: 77.93-7.95 (m, 2H), 7.49-7.52 (dd, J = 8.5, 2.5 Hz,1H), ] 7.19-7.21 (d,J = 8.5 Hz,1H), 7.04-7.07 (m, 2H), 5.25-5.28 (d,J = 12.2 Hz, 1H), 4.77-4.80 (d, J = 12.2 Hz, 1H), 4.44-4.46 (m, 2H), 4.23-4.25 (t, J = 4.8 Hz, 2H), 3.90-3.92 (t, J = 4.8 Hz, 2H), 3.73-3.79 (m, 4H), 3.65-3.71 (m, 6H), 2.82 (s, 4H), 1.35 (s, 9H).
13C-NMR: 168.72, 162.19, 160.53, 152.81, 151.81, 148.13, 144.18, 142.35, 140.78, 135.61, 131.21, 130.80, 122.14, 117.99, 117.52, 117.47, 117.19, 114.82, 78.88, 71.09, 70.95, 70.81, 70.43, 69.62, 68.52, 68.14, 34.75, 31.52, 25.64.
ESI HRMS: calcd. (M+H+): C33H38NO11+: 624.2439, found 624.2442.
13C-NMR: 1846 cm-1 (v C=O).
Storage: +10C, Protect from light
Shipped: Ambient Temperature
Provider
From the laboratory of Vladimir V. Popik, PhD, University of Georgia.
References
  1. Matthew Bjerknes, Hazel Cheng, Christopher D. McNitt, and Vladimir V.Popik: Facile Quenching and Spatial Patterning of Cylooctynes via Strain-Promoted Alkyne–Azide Cycloaddition of Inorganic Azides. Bioconjugate Chem., 2017, 28 (5), pp 1560–1565
  2. Orski, SV, Poloukhtine, AA, Arumugam, S, Mao, L, Popik, VV, Locklin, J: High density orthogonal surface immobilization via photoactivated copper-free click chemistry: (2010) J. of the Am. Chem. Soc. 132(32) 11024-11026
  3. Selvanathan Arumugam, Sara V. Orski, Ngalle Eric Mbua, Christopher McNitt, Geert-Jan Boons, Jason Locklin, and Vladimir V. Popik: Photo-click chemistry strategies for spatiotemporal control of metal-free ligation, labeling, and surface derivatization. Pure Appl. Chem., Vol. 85, No. 7, pp. 1499–1513, (2013)
  4. US Patents US8,258,347, US8,426,649 and US8,541,625

If you publish research with this product, please let us know so we can cite your paper.

 
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